The carbon-Ferrier rearrangement: An approach towards the synthesis of C-glycosides

Abstract

The carbon-Ferrier rearrangement is the reaction of appropriately functionalised glycals, with a variety of carbon nucleophiles such as allyltrimethylsilanes, alkynyltrimethylsilanes, silyl cyanides etc. involving the corresponding nucleophilic addition at the anomeric carbon with concomitant loss of a substituent at C-3. This leads to double bond migration to give 2,3-unsaturated sugars which act as useful chiral substrates for further manipulations in organic synthesis.